Lindsay Lohan Ch. 03

Toby originally thought Dina was joking with him but then she had produced contracts and documents which Toby had to sign. In truth Toby had dreamed of fucking Lindsay and would have offered his services for free but to also get paid for it all seemed like some kind of fantasy.

That was until he walked into this house and they found Lindsay on the floor. Toby had thought Lindsay looked hot laying on the floor in her black bathing suit but even to him it was clear she was really drunk and Toby was now having major second thoughts about the whole thing.

Just as Toby was thinking about heading for the door and running home Dina Lohan returned to the living room heading for the kitchen. Dina was wearing a sleeveless black dress which ended just above her knees. As she walked into the kitchen she opened a cupboard and reached up to grab something. As she reached up Toby noticed that Dina had great legs for a woman of her age.

"We'll be with you in a minute Toby honey." Said Dina as she walked past him heading back to the bathroom. Toby didn't know what the next hour might bring but he decided to hang around and find out.

Back in the bathroom Dina handed her daughter two headache tablets which she had collected from the kitchen. Lindsay washed them down with water and waited for her head to clear a little.

"Who is out there?" she asked her mother.

"Toby Garrett." Said Dina "You remember Toby don't you?"

"Ali's friend Toby?" said Lindsay quite shocked.

"Yeah that's him." Said Dina matter of factly. "Don't worry he signed all the contracts."

"You hired one of Ali's friends to come over here and make this video with me?"

"You said to get someone we could trust." Argued Dina.

"You expect me to fuck one of my younger sister's friends?" asked Lindsay now getting cross.

"Who was I going to find on such short notice?" asked Dina.

"Is he even old enough?" questioned Lindsay.

"He's 19 Lindsay. I told you we checked all that when we got him to sign the contract."

"So he wants to do this?" asked Lindsay.

"Of course." Said Dina "Why wouldn't he?"

"Fuck," said Lindsay "I haven't seen Toby since he was a little kid playing with Ali."

"Well he's all grown up now." Said Dina "He's perfect. He's young, he's good looking, and he's a decent guy who we can totally trust. I know his mother."

"Does Ali know about any of this?" asked Lindsay.

"No of course not." Said Dina "But Ali and Toby aren't as close as they used to be anymore."

Lindsay sat on the toilet and thought about it for a few minutes. Everything about this felt wrong from the start but it was too late to stop it now. Lindsay gave a resigned sigh and stretched her neck. The tablets were starting to work and Lindsay's head was beginning to clear a little.

"Ok." Said Lindsay "Whatever. Let's get this over with shall we?"

Dina smiled and said "That's my girl."

"So how are we going to do this?" asked Lindsay "Where's the camera?"

"Toby has the camera." Said Dina.

"Ok and he's going to shoot this like it was a home sex movie?" Asked Lindsay.

"Kind of." Said Dina "But we don't want one of those shaky out of focus movies. The guys at the porn studio were very clear that they wanted steady shots."

"Does Toby know anything about filming?" asked Lindsay.

"Don't worry about it." Said Dina calmly "I'm going to be in charge of shooting this movie."

"Your going to shoot it?" exclaimed Lindsay with surprise.

"Yes." Said Dina "It's the only way to make sure we get decent material. You don't want to have to do a reshoot on another day do you?"

"No." said Lindsay "But I don't want to have sex with my fucking mother taping it on camera either."

"Relax honey." Said Dina "I'm not actually going to be filming it. I'll just set the camera up and make sure it's a good angle. Then we'll shoot a little. Stop. Move the camera. Shoot a little more. Remember we are only looking for like 15 minutes of footage."

"But you are planning to be in the room while I have sex with Toby?" asked Lindsay.

"Yes." Said Dina without hesitation "Like I said I have to make sure we get good footage."

Lindsay couldn't believe her ears. First she was being forced into cheating on Sadie. Then she was going to have to cheat with a close friend of her little sister's and now she was going to have to do it with her mother supervising everything. How much worse can this deal get wondered Lindsay.

"You don't think that's a little weird? You watching me have sex?" asked Lindsay.

"Honey I'm not going to be watching really." Said Dina "Just supervising the camera."

Dina laughed and tried to reassure her worried daughter. "You seem to be forgetting Lindsay that I've seen you naked thousands of times. I gave birth to you. Bathed you. Wiped your ass."

"When I was a kid sure. But I'm older now. It's different." Said Lindsay.

"I saw you naked a little while ago when you shot Playboy. I was there at that shoot remember."

"I guess." Sulked Lindsay "But this feels different. I'm going to be having sex."

"It's not real sex Lindsay." Argued Dina "It's just going through the motions for 15 minutes. It'll be just like the Playboy shoot with me in the background supervising."

Lindsay wanted to argue further but it seemed like delaying the inevitable and her head had cleared quite a bit so maybe it was just better to stop talking and just get on with it. After all it was just another acting job to Lindsay. Lindsay stood up from the toilet and was a little surprised to find her legs were still a little shaky. She took a couple of steps forward though and seemed to fine. Certainly the alcohol had worn off quite a bit and Lindsay felt sure she could endure what the next few minutes had in store for her.

"Are you ready?" asked Dina

"As I'll ever be." Said Lindsay walking toward the bathroom door.

By this time Toby had taken a seat on Lindsay's couch. He was thinking about Lindsay Lohan who he knew as a kid growing up. Lindsay had always been Ali's older famous sister and Toby had always had the biggest crush on her. The first time he had masturbated was thinking about Lindsay and even now several years later if you checked Toby's closet you would find hidden away a copy the Lindsay Lohan playboy issue.

Toby's concentration was broken as he heard a noise and turned in his seat to see Lindsay Lohan walk into the room. She looked a lot better and even though she might have been a little unstable on her feet still it was clear she had sobered up a lot since Toby and Dina had found her on the floor when they first walked into the house.

"Hi Toby." Said Lindsay "How are you?"

"I'm good." Replied Toby "Are you feeling better?"

Lindsay ignored that question and strode around to sit opposite Toby. As she walked past him Toby had a moment to gaze upon Lindsay's slim and toned legs which were quite pale but covered in freckles. Lindsay was barefoot and only wearing a black one piece bathing suit.

As Lindsay took a seat Toby then found himself watching Dina Lohan walk around him. Dina was wearing a black dress but Toby could see that Dina also had very toned legs and Toby could see where Lindsay got her looks from.

The three of them kept quiet as Dina picked up the video camera and began to set it up. She'd already previously set the date to over a year ago and now she began to look around the room for a good place to put the camera.

Dina placed the camera on a table and looked through the viewer to check she had a good angle on Toby. Satisfied that everything looked good Dina turned back to Lindsay and Toby and explained what was going to happen next.

"Ok." Said Dina "Toby you stay where you are I've got the camera perfect on you. Lindsay I need you to come over and kneel in front of Toby."

Lindsay said nothing but slowly got up from her seat and walked across to Toby. She crouched down in front of him on the floor. Dina took another look in the viewer of the camera. From this angle she had a perfect shot on both Toby and Lindsay.

"That's great." Said Dina "OK so there's no easy way of saying this so I'll just tell you what's needed."

Both Lindsay and Toby looked over at Dina. Both of them knew what was coming but it was still a shock to hear Dina give words to it.

"Lindsay, I want you give Toby a blow job. I'll wait until he's hard then I'll turn on the camera. I figure we do 5 minutes of that. Then that's done."

Toby was shocked by how professionally Dina was directing all this. Lindsay was actually relieved by her mother's all business no nonsense approach. It was exactly what Lindsay wanted.

"Now remember the golden rule." Said Dina "Under no circumstances do either of you acknowledge my presence in the room. I'll be behind the camera but at no time look at me or talk to me. To anybody watching this video it has to look like it was just the two of you alone."

Both Lindsay and Toby nodded their heads at Dina and then looked at each other. There was a silent understanding between the two of them.

"Ok," said Dina "You can start now and I'll turn on the camera as soon as Toby is hard."

"That won't be long Dina." Said Toby reaching down to rub the bulge in his pants "I'm already pretty much there."

"Are you ready Lindsay?" asked Dina

"I'm ready Dina." Said Lindsay calling her mother by her name for the first time ever.

Dina was surprised by Lindsay using her name but figured maybe it was best for the next few minutes if she was just Dina and not mom.

"Then action." Said Dina stepping behind the camera.

The actress in Lindsay took control and she snapped into character. This would all be over in a few minutes thought Lindsay using her hands to unzip the front of Toby's pants. This was not about pleasure or sex thought Lindsay now tugging his pants down towards Toby's ankles. This was just an acting job Lindsay thought as she hooked her fingers into Toby's underwear and pulled them down.

As Lindsay pulled the underwear down to Toby's ankles she looked up and for the first time saw Toby's cock already half raised. The cock was not just big it was without doubt the biggest cock Lindsay had ever seen.

"Fuck." Shouted Lindsay "Cut Dina."

"I haven't turned the camera on yet Lindsay." Explained Dina.

"Look at his fucking cock?" exclaimed Lindsay "What am I supposed to do with that. It's a fucking monster."

Dina at Toby's cock and had to agree with her daughter's opinion. It was indeed a very large penis. It was at least 8" long already and not yet fully hard. Dina guess that once it got fully hard it could well be close to 12" long.

"Just do your best Lindsay." Said Dina.

Lindsay silently cursed Dina but proceeded to do as asked. She turned back towards Toby who looked visibly smug at Lindsay's reaction to the size of his cock. Lindsay reached out a hand and grasped Toby's cock noting that already her hand could not reach completely around it.

Lindsay began to jerk the cock in her hand. Slowly moving her hand up and down the length of it. Already she could feel the cock growing harder and larger. She increased the momentum of the jerking and Toby released a sigh of satisfaction watching the Hollywood star jerk him off.

After a couple of minutes Lindsay stopped jerking Toby off and released his cock. There it stood completely upright and stiff as can be slightly twitching as it swayed in the air. The cock was at least 12" long and Lindsay had no idea a cock could be so thick.

Lindsay was about to complain to Dina that there was no way she was going to be able to have sex with a cock that size but changed her mind. What was the point of bitching about it? She might just as well do her best and get this over as soon as possible.

She spat out a big dollop of spit which landed on the big purple head of Toby's cock. The spit slowly began to drip down the length of his cock. Before it reached the bottom of the shaft though Lindsay reached up and took the top of the cock in her mouth.

It was the first blow job Lindsay had given since that day with Earl the old judge. Lindsay had to open her mouth as wide as possible just to get the head inside. Once she had managed that though she slowly began to drop her mouth down the shaft until she felt Toby's cock touch the back of her throat.

Dina watched from behind the camera. She saw Lindsay really struggling to suck Toby's penis and for the first time felt shame. What was doing to her oldest daughter thought Dina as she reached down and switched the video camera on to start recording.

Lindsay engorged cock probing at the back of Lindsay's throat induced her into gagging and as she did spit burst out of her mouth and down Toby's cock. Lindsay also felt her eyes begin to water.

Toby meanwhile found himself enjoying probably the best blow job of his young life. He could not believe how sexy it was to watch Lindsay Lohan suck his cock. Her beautiful red lips travelled up and down his cock as far as they could but Toby wanted more. Toby wanted his entire cock inside Lindsay's mouth not just the top half.

Lindsay felt a hand on the back of her head and realised that Toby was now pushing her head further down the shaft of his cock. He was also gently thrusting his hips to raise up causing the cock to do deeper into her mouth. Each time the cock hit the back of Lindsay's mouth she would gag and the produce yet more saliva lubrication.

Toby continued to use his hand to push Lindsay's mouth deeper onto his now throbbing cock. It felt so good and he had to get as much of it inside her mouth as he could. He grabbed a tight hold of that famous red hair and used it to dictate the pace of Lindsay's blow job.

Dina watched from behind the camera and felt a mixture of shame and pride. She felt shame because what she was watching went against all her maternal instincts but pride because Lindsay really was being a trooper and was actually doing a good job with that massive penis. Dina checked the video camera and decided a couple more minutes would be enough and the blow job part of this video would be over.

Toby felt the mouth on his cock and threw his head back to look at the ceiling. It was so amazing that he could feel his balls ache to spunk out his cum. But suddenly all too soon that felt like it actually was going to happen. Toby grunted as he felt his cum suddenly rise and he tried his hardest to hold it back knowing it was too soon for the video.

Lindsay continued sucking Toby now wondering how much longer the blow job part of this video would last. It was no fun to Lindsay trying to suck this cock. Her jaw ached, her eyes were watering and the back of her throat felt sore. Plus his fucking hand had too tight a grip in her hair and when her mother finally called cut Lindsay was going to have a few things to say to young Toby.

Then all of a sudden Lindsay felt the first spurt of cum hit the back of her throat. It was quickly followed by a second and third and Lindsay realised that Toby was blowing his load in her mouth. She immediately tried to remove her mouth but Toby's hand held her head in place and Lindsay continued to feel spurts of cum entering her mouth.

"Fuuuuucccckkkkkkkk." Cried Toby as Lindsay felt her mouth filling with cum.

Dina realised what was happening too late to call cut. She could see Toby tense up and then spasm in ecstasy while poor Lindsay tried to pull away but was held in place by Toby's hands. Lindsay actually looked like she was starting to choke and Dina knew she had to stop this now.

Dina reached over and turned off the video camera. "And Cut." She yelled to both Toby and Lindsay. Toby released Lindsay's head and Dina watched as her daughter fell onto the floor and coughed up mouthfuls of spunk.

"He nearly fucking killed me." Grasped Lindsay between her coughing and spluttering.

"Why did you cum Toby?" asked Dina knowing she only had a few minutes of usable footage.

"I didn't mean to." Said Toby "but it felt so good I couldn't stop it."

"You fucking cunt." Yelled Lindsay while spitting what was left of his cum onto the floor.

"I'm sorry Lindsay." Apologised Toby.

Dina knelt down beside her daughter and gently rubbed her back. "You did really good honey." She said gently to Lindsay. "Are you ok?" Dina asked now brushing some hair out of Lindsay's face.

Lindsay managed to sit down on the floor and regained some composure. "I guess I'm ok but I'm glad that it's over." She said.

"If we edit out the beginning and the unfortunate premature ending then I think we have at least 5 minutes of footage we can use." Said Dina "We'll take a short break and come back to shoot 10 minutes of sex and then we are done."

"I'm not fucking that asshole Dina." Shouted Lindsay "Or his mutant dick."

"Honey we need to finish this or else its worthless." Reasoned Dina.

"He fucking came already." Said Lindsay "It's over whether you like it or not."

Dina looked over to Toby who was breathing heavily himself. Between his legs sat his now flaccid penis covered in cum and Lindsay's saliva. He actually looked quite concerned as if he had let everybody down and maybe a little shamed over his premature ejaculation.

"Toby, honey do you think you can go again?" asked Dina.

"I think so." Said Toby who at 19 was actually quite used to cumming more than once a night.

"I need a break." Said Lindsay from the floor. "I'm going to the bathroom to freshen up when I come back I he better be hard and ready to go again. One way or another this is all over in 20 minutes."

Lindsay got up from the floor and stomped off towards the bathroom. She didn't look back at either Toby or her mother and slammed the bathroom door once she was inside.

"Toby honey you need to get hard again real quick before she comes backs." Warned Dina. "I know my daughter and she is about to have a fit and throw both of us out of here."

Toby immediately grasped his flaccid penis and tried to masturbate with it. It was still sticky with cum and spit but would not waken from its floppy sleep. He increased the speed of the strokes but sill nothing was happening.

"It usually takes about 15 minutes to go again." Warned Toby frantically pounded his completely flaccid cock.

"We don't have 15 minutes honey." Said Dina "She'll be back any minute and if you're not hard already she will go nuts and throw a fit."

"Help me then." Begged Toby.

"How?" Dina asked not comprehended what he meant.

"Some me something that normally helps." Said Toby.

"Like what?" asked Dina still in the dark to what Toby was suggesting.

"Lift up your skirt and show me your panties." Pleaded Toby.

Dina gasped at the request. Was he serious? Dina never thought for a second that seeing her panties might help this young teenager gain an erection.

"Toby honey, I'm 50 years old. I got four kids. I'm not going to lift up my skirt so some teenager can jerk off while looking at me."

Toby looked disappointed but continued his best to get himself hard. Dina watched him jerk his hand hard and fast. His penis was now dried and it looked like it was beginning to turn red and chafe but still it remained soft and useless. Dina knew Lindsay would be back any moment and if they were not ready to shoot it would all be over.

Dina considered her options and even though it felt degrading to her to reached down with both hands and grasped the bottom of her skirt. Then she quickly lifted it up over her thighs to her waist revealing a pair of white panties.

Toby took in the view of Dina Lohan standing before him showing off her panties. Was this woman really 50 he wondered looking at her beautiful thin legs. She was a little more tanned then Lindsay but Toby could see that Dina too had beautiful freckles along her legs.

Looking at the white panties too revealed a dark colour underneath and a camel toe outline of Dina's pussy. Toby began to feel his cock stir in his hand. A tiny encouragement of hardness returning to it.